Halogen Bonding Interactions in DDQ Charge Transfer Salts with Iodinated TTFs

International audienceOxidation of 3,4-ethylenedithio-3'-iodo-tetrathiafulvalene (EDT-TTF-I) and 3,4-ethylenedithio-3',4'-diiodo-tetrathiafulvalene (EDT-TTF-I2) with DDQ afforded two different salts formulated as (EDT-TTF-I)(DDQ) and (EDT-TTF-I2)2(DDQ)*(CH3CN), both characterized with a full charge transfer to the DDQ acceptor moiety and by short and linear halogen bonding interactions between the iodine atom as halogen bond donor, and the carbonyl oxygen or the nitrile nitrogen atoms of reduced DDQ

C--I NC halogen bonding in two polymorphs of the mixed-valence 2:1 charge-transfer salt (EDTTTF- I2)2(TCNQF4), with segregated versus alternated stacks

International audienceOxidation of diiodoethylenedithiotetrathiafulvalene (EDT-TTF-I2), C8H4I2S6, with the strong oxidizer tetrafluorotetracyanoquinodimethane (TCNQF4), C12F4N4, affords, depending on the crystallization solvent, two polymorphs of the 2:1 charge-transfer salt (EDT-TTF-I2)2(TCNQF4), represented as D2A. In both salts, the TCNQF4 is reduced to the radical anion state, and is associated through short C-I...NC halogen bonds to two EDT-TTF-I2 molecules. The two polymorphs differ in the solid-state association of these trimeric D-A-D motifs. In polymorph (I) the trimeric motif is located on an inversion centre, and hence both EDT-TTF-I2 molecules have +0.5 charge. Together with segregation of the TTF and TCNQ derivatives into stacks, this leads to a charge-transfer salt with high conductivity. In polymorph (II) two crystallographically independent EDT-TTF-I2 molecules bear different charges, close to 0 and +1, as deduced from an established correlation between intramolecular bond lengths and charge. Overlap interactions between the halogen-bonded D0-A^{{-}{\bullet}}-D^{{+}{\bullet}} motifs give rise, in a perpendicular direction, to diamagnetic A22- and D0-D22+-D0 entities, where the radical species are paired into the bonding combination of respectively the acceptor LUMOs and donor HOMOs. The strikingly different solid-state organization of the halogen-bonded D-A-D motifs provides an illustrative example of two modes of face-to-face interaction between [pi]-type radicals, into either delocalized, uniform chains with partial charge transfer and conducting behaviour, or localized association of radicals into face-to-face A22- and D22+ dyads

Feasibility study thin glasses for greenhouse roof designs

In this study, the feasibility of the application of flexible thin glass in greenhouses was investigated. With the development of thin but very strong glass plates like for mobile phones, new possibilities are being created for new greenhouse roof designs, the usage in multi-layered glass roof give possibilities for high-insulation greenhouse coverings. Flexible thin glass is a tempered glass. While standard tempered glass goes through a thermal process, this is a chemical process, which makes the glass five times stronger, creating the possibility of thickness reduction and bending. By adding nanocoatings the reflection can be reduced and the light transmission can be increased. Multi-layered greenhouse roofs can be created, resulting in a higher light transmission than currently available multilayer polycarbonate (PC) sheets, but also a higher transmission than today’s insulating double glass. The study shows that such glass combinations lead to an additional 20% energy savings based on heat demand for Phalaenopsis. Thin glasses are particularly strong and can also be used in curved form. This makes new greenhouse roof designs with these glasses possible. Especially the low weight offers advantages here. Important mechanical aspects and bottlenecks for the use in greenhouses have been mapped out. Due to limitations in today’s available dimensions and high prices, the use of thin glass in greenhouses will be further away in the futur

Feeding Cyprinus carpio with infectious materials mediates cyprinid herpesvirus 3 entry through infection of pharyngeal periodontal mucosa

Cyprinid herpesvirus 3 (CyHV-3), also known as Koi herpesvirus, is the etiological agent of a mortal disease in common and koi carp. Recently, we investigated the entry of CyHV-3 in carp using bioluminescence imaging and a CyHV-3 recombinant strain expressing luciferase (LUC). We demonstrated that the skin is the major portal of entry after inoculation of carp by immersion in water containing CyHV-3. While this model of infection mimics some natural conditions in which infection takes place, other epidemiological conditions could favour entry of virus through the digestive tract. Here, we investigated whether ingestion of infectious materials mediates CyHV-3 entry through the digestive tract. Carp were fed with materials contaminated with the CyHV-3 LUC recombinant (oral contamination) or immersed in water containing the virus (contamination by immersion). Bioluminescence imaging analyses performed at different times post-infection led to the following observations: (i) the pharyngeal periodontal mucosa is the major portal of entry after oral contamination, while the skin is the major portal of entry after contamination by immersion. (ii) Both modes of inoculation led to the spreading of the infection to the various organs tested. However, the timing and the sequence in which some of the organs turned positive were different between the two modes of inoculation. Finally, we compared the disease induced by the two inoculation modes. They led to comparable clinical signs and mortality rate. The results of the present study suggest that, based on epidemiological conditions, CyHV-3 can enter carp either by skin or periodontal pharyngeal mucosal infection

Skin mucus of Cyprinus carpio inhibits cyprinid herpesvirus 3 binding to epidermal cells

Cyprinid herpesvirus 3 (CyHV-3) is the aetiological agent of a mortal and highly contagious disease in common and koi carp. The skin is the major portal of entry of CyHV-3 in carp after immersion in water containing the virus. In the present study, we used in vivo bioluminescence imaging to investigate the effect of skin mucus removal and skin epidermis lesion on CyHV-3 entry. Physical treatments inducing removal of the mucus up to complete erosion of the epidermis were applied on a defined area of carp skin just before inoculation by immersion in infectious water. CyHV-3 entry in carp was drastically enhanced on the area of the skin where the mucus was removed with or without associated epidermal lesion. To investigate whether skin mucus inhibits CyHV-3 binding to epidermal cells, tail fins with an intact mucus layer or without mucus were inoculated ex vivo. While electron microscopy examination revealed numerous viral particles bound on the fins inoculated after mucus removal, no particle could be detected after infection of mucus-covered fins. Finally, anti-CyHV-3 neutralising activity of mucus extract was tested in vitro. Incubation of CyHV-3 with mucus extract reduced its infectivity in a dose dependent manner. The present study demonstrates that skin mucus removal and epidermal lesions enhance CyHV-3 entry in carp. It highlights the role of fish skin mucus as an innate immune protection against viral epidermal entry

Benzodithiophene and benzotrithiophene as \ucf\u80 cores for two-and three-blade propeller-shaped ferrocenyl-based conjugated systems

The syntheses of linear and star-shaped bis- and tris(ferrocenyl) derivatives of benzo[1,2-b:4,5-b\u2032]dithiophene and benzo[1,2-b:3,4-b\u2032:5,6-b\u2032\u2032]trithiophene are achieved through one-pot CuI/TMEDA-catalyzed (TMEDA = tetramethylethylenediamine) multiple annulations of bromoethynylbenzenes with sodium sulfide. In addition, the preparation of the parent benzotrithiophene in a good yield with a short reaction time is achieved through the threefold annulation of 1,3,5-trifluoro- Introduction Benzo[b]thiophene (BT, Scheme 1) and its derivatives are an important class of fused thiophene compounds owing to their wide range of biological properties[1,2] and various applications in materials science.[3] Scheme 1. Fused thiophene compounds: benzo[b]thiophene (BT), benzo- [1,2-b:4,5-b\u2032]dithiophene (BDT), and benzo[1,2-b:3,4-b\u2032:5,6-b\u2032\u2032]trithiophene (BTT). In particular, (multi)thiophene fused aromatic compounds are attracting interest as promising electronic materials for organic conductors,[4] organic light-emitting diodes,[5] photovoltaic cells,[6] and field-effect transistors.[7] For this reason, thiophene- based \u3c0-conjugated oligomers have been investigated widely as organic semiconductors.[8] Recently, much effort has been focused on benzo[1,2-b:4,5-b\u2032]- dithiophene (BDT) and benzo[1,2-b:3,4-b\u2032:5,6-b\u2032\u2032]trithiophene (BTT, Scheme 1) as potential \u3c0 cores for a new class of organic semiconductors as they contain two or three identical thiophene moieties with C2h or C3h symmetries that enable twoand three-dimensional molecular extensions. [a] Department of Chemical Sciences, University of Padova Via Marzolo 1, 35131 Padova, Italy E-mail: [email protected] http://www.chimica.unipd.it/ Supporting information and ORCID(s) from the author(s) for this article are available on the WWW under https://doi.org/10.1002/ejoc.201701045. Eur. J. Org. Chem. 2017, 5966\u20135974 5966 \ua9 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2,4,6-tris(trimethylsilyl)ethynylbenzene. The computed structural and electronic features of these ferrocenyl derivatives as well as their UV/Vis spectra and electrochemistry are discussed, and the results provide insights into the effect of the presence of three rather than two ferrocenyl units. To the best of our knowledge, 2,5,8-tris(ferrocenyl)benzo[1,2-b;3,4-b\u2032;5,6-b\u2032\u2032]trithiophene is the first organometallic complex containing benzotrithiophene

Skin mucus of Cyprinus carpio inhibits cyprinid herpesvirus 3 binding to epidermal cells

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